Rice K C, Shiotani S, Creveling C R, Jacobson A E, Klee W A
J Med Chem. 1977 May;20(5):673-5. doi: 10.1021/jm00215a011.
The reaction of N-2,4,5-tribenzyloxyphenyl)ethyl methanesulfonate, prepared in a seven-step sequence, with normetazocine followed by hydrogenolysis of the benzyloxy-protecting groups, gave N-(2,4,5-trihydroxyphenethyl)normetazocine. This compound was prepared to study the effect of a narcotic analgesic containing a functional group which could be activated in situ to a moiety potentially capable of reacting irreversibly with the narcotic receptor. This 6-hydroxydopamin derivative of normetazocine did not prove to be a useful affinity label. Its low toxicity could indicate the necessity for the formation of an aminochrome system for the expression of toxicity by 6-hydroxydopamine.
通过七步反应序列制备的甲磺酸 N-(2,4,5-三苄氧基苯基)乙酯与去甲美沙酮反应，随后对苄氧基保护基团进行氢解，得到 N-(2,4,5-三羟基苯乙基)去甲美沙酮。制备该化合物是为了研究一种含有官能团的麻醉性镇痛药的作用，该官能团可在原位被激活为可能与麻醉受体发生不可逆反应的部分。去甲美沙酮的这种 6-羟基多巴胺衍生物并未被证明是一种有用的亲和标记物。其低毒性可能表明需要形成氨基色素系统才能使 6-羟基多巴胺表现出毒性。
